IMPPAT Phytochemical information: 
gamma-Hydroxy-L-arginine
gamma-Hydroxy-L-arginine
Summary

SMILES: OC(C[C@@H](C(=O)O)N)CN=C(N)N
InChI: InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)/t3?,4-/m0/s1
InChIKey: OPCBKDJCJYBGTQ-BKLSDQPFSA-N
DeepSMILES: OCC[C@@H]C=O)O))N)))CN=CN)N
Functional groups: CO; CC(=O)O; CN; CN=C(N)N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Amino acids and Peptides
NP Classifier Superclass: Small peptides
NP Classifier Class: Aminoacids
Synonymous chemical names:
(2s,3r)-4-hydroxyarginine, gamma-hydroxyarginine, 2(s),4(r)-4-hydroxyargenine
External chemical identifiers:
CID:CID_164980; ChEBI:CHEBI:47815; FDASRS:LT9MLJ6CFA; SureChEMBL:SCHEMBL296234
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
gamma-Hydroxy-L-arginine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 190.2
Log P RDKit -2.58
Topological polar surface area (Å2) RDKit 147.95
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 6
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 0
gamma-Hydroxy-L-arginine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.237362
gamma-Hydroxy-L-arginine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.13
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No